Substantive orthooxyazo dyestuffs and a process of making same.



Enemv' annnnwnnr, HERMAN rnrrzscne, AND nnmnrcn scnonnn, or nAsEL, swrrznnnmn, assreuons r SOCIETY or cnemrcar. mnusrnv m BASLE, or

BASED, SWITZERLAND.

suns rm'rlvn OBTHOOXYAZO DYESTUFFS AND A PROCESS or MAKING sn.

80 Drawing.

To all whom it may concern Be it known that we, EUGEN ANDERWERT, HERMAN FRITZSCHE, and HEINRICH SGHOBEL,

- all three chemists and citizens of the Swiss a I on 311, /CHB\NH, or x on xm wherein X stands for a diphenyl-binding or one of the groups" me: o

co, NH, 0-0,!15-0, 02m NH 0 As parent materials corresponding to the given formulas can be employed for instance the following compounds and their derivatives viz:

the o-o- (3.3 -dioxybenzidin:

' m1 -Nn,,

q a the diamidodioxydiphenylmethane:

CH CO Specification of Letters Patent.

Patented Jan. 2, 1917.

Application filed October 8, 1915. Serial No. 54,891.

the diamidodioxydiphenylurea:

\NH NH,

on the diamidodioxydiphenylketone:

the diamidodioxydiphenylamin:

m1 NH um,

the hydroquinon-p-p-diaminodioxydiphenylether 7 5 the diamidodioxy-p-p-diphenylethylenether:

The nev dyestuffs are intensely colored powders yleldlng wlth concentrated sulfuric acid strongly, colored solutions and dissolving in water with red to yellow and violet colorations, which are intensivelychan ed by add1t1on of sodium carbonate or 0% soda'lye and dyeing cotton, wool, silk, mixed goods,

straw, wood and paper various tints according to the methods used for the known substantive dyestufi's.

The process is illustrated by the following examples:

Example 1: 21.6 kg. o-o- (3-3')-dioxybenzidin (obtained by condensation of orthonitrophenol with formaldehyde and subsequent reduction) are transformed in the usual manner into the corresponding tetrazo derivative. This latter is pdured into a solution of 50 kg. 2:5:7 aminonaphtholmonosulfonic acid and 50 kg. sodium carbonate in water. The combination occurs slowly and is at the end aided by a feeble warming. The

dyestuif isolated in the usual manner dyes cotton deep blue-roseate.

Example 3: 43.4 kg. diaminodiphenyl- I ureadisulfonic acid carbonate.

(obtained by introducing phosgen- (carbonyl chlorid) into an alkaline solution of 2-nitro- 4-amino-1-phenol-6-sulfonic acid and reduccarbonate and tetrazotized with 60 kg. hydrochloric acid and 14 kg. sodium nitrite and the resulting tetrazo derivative is combined with k meta-aminobenzoyl-2:5:7-aminonaphtho sulfonic acid and 60 kg. sodium The following day the mass is mg subsequently) are dissolved with sodium heated to 40 C. and the dyestuif salted out and isolated in the usual way. It dyes cotton a dull lilac.

The new dyestuffs dye cotton, 'wool, silk, mixed goods, straw, wood, paper, leather, etc, like the known substantive dyestufi's 70 and can be employed for the production of' lakes and as parent materials for the production of new valuable derivatives.

What we claim is: v V

1. The described process for the manufacture of new substantive orthooxyazo dyestufi's consisting in combining the orthooxytetrazo derivatives of the orthoaminophelnol derivatives corresponding'to the formu a (wherein X stands for a diphenyl-binding or I one of the groups CO, NH, 0-653, c2114 with 2:5:7 -amino1iaphtholsulfonic com- 7 pound.

2. The described process for the manufacture of new substantive orthooxyazo d estufi's consisting in combining the ort ooxytetrazo derivatives of the orthoaminophelnol derivatives corresponding to the formu a and X \M Go fi I oxyazo dyestufl's corresponding to. the formula n and on 0.H. Ckm-u-u-Y (wherein X stands for a diphenyl-binding or one of the'groups I cm, 0 co, m1, o-omi-d, cm/ 2 Nn o and Y for a sulfo derivative of 2:5-aminonaphthol containing a sulfo group in the 7- position), which constitute intensely colored powders yielding with concentrated sulfuric acid intensely colored solutions and dissolving in water with red and yellow to violet colorations which are intensively changed by addition of sodium carbonate or of sodalye and dyeing cotton, Wool, silk, mixed goods, straw, wood and paper various tints according to the methods used for the known substantive dyestufi's.

In witness whereof we have hereunto signed our names this 17th day of September 1915, in the presence of two subscribing witnesses.

EUGEN ANDERWERT. DR. HERMAN FRITZSCHE. DR. HEINRICH SCHOBEL. \Vitnesses:

ARNOLD ZUBER, AMAN I. RILLEY. 

